HCID 12753707, compound → [3-(9H-Carbazol-9-YL)propyl]phosphonic acid

Participants

Reaction Steps

Trimethylsilyl(TMS)-bromide (1.12 mL, 8.67 mmol) was added via syringe to a solution of diethyl 3-(9H-carbazol-9-yl)propylphosphonate (1.00 g, 2.89 mmol) in ˜20 mL dry DCM in a 50 mL rbf. The flask was greased and capped and allowed to stir for 90 minutes. The volatile organics were removed under vacuum and 30 mL of 1:1 MeOH:H2O were added. The solution turned a cloudy whitish/grey. The solvents were removed and the product recrystallized from 2:1 H2O:acetone (grey powder, 612 mg) and 1:1 H2O:MeOH (PJH-II-5c, glassy grey solid, 42 mg). Both recrystallization solvents yielded pure product. Total yield was 78%. 1H NMR (400.14 MHz, DMSO) δ 8.15 (d, J=8.00 Hz, 2H), 7.65 (d, J=8.00 Hz, 2H), 7.45 (dt, J=15.41, 1.00 Hz, 2H), 7.19 (t, J=14.81 Hz, 2H), 4.48 (t, J=13.60 Hz, 2H), 2.03-1.89 (m, 2H), 1.59-1.46 (m, 2H). 13C{1H} NMR (100.62 MHz, DMSO) δ 140.01 (2C), 125.76 (2C), 122.07 (2C), 120.33 (2C), 118.78 (2C), 108.33 (2C), 42.48 (d, J=17.31 Hz), 25.00 (d, J=137.35 Hz), 22.67 (d, J=4.13 Hz). 31P{1H} NMR (161.97 MHz, DMSO): δ 26.78. Analysis found (calculated) %: C, 62.27 (62.28); H, 5.56 (5.58); N, 4.73 (4.84). MS (FAB, m/z): 290 ([M+H]+, 100%). Exact mass found (calculated for [M+H]+, m/z): 290.09405 (290.09461).

Provenance & Evidence